US6960410B2 - Electrolyte comprising non-ionic surfactant and lithium ion battery using the same - Google Patents

Electrolyte comprising non-ionic surfactant and lithium ion battery using the same Download PDF

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US6960410B2
US6960410B2 US10/380,141 US38014103A US6960410B2 US 6960410 B2 US6960410 B2 US 6960410B2 US 38014103 A US38014103 A US 38014103A US 6960410 B2 US6960410 B2 US 6960410B2
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electrolyte
lithium ion
ion battery
group
lithium
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US20030170547A1 (en
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Hyeong-Jin Kim
Yeon-Hee Lee
Bong-Youl Chung
Young-Keun Kim
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LG Chem Ltd
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LG Chem Ltd
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/58—Selection of substances as active materials, active masses, active liquids of inorganic compounds other than oxides or hydroxides, e.g. sulfides, selenides, tellurides, halogenides or LiCoFy; of polyanionic structures, e.g. phosphates, silicates or borates
    • H01M4/583—Carbonaceous material, e.g. graphite-intercalation compounds or CFx
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
    • H01M4/131—Electrodes based on mixed oxides or hydroxides, or on mixtures of oxides or hydroxides, e.g. LiCoOx
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
    • H01M4/485—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of mixed oxides or hydroxides for inserting or intercalating light metals, e.g. LiTi2O4 or LiTi2OxFy
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
    • H01M4/50—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of manganese
    • H01M4/505—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of manganese of mixed oxides or hydroxides containing manganese for inserting or intercalating light metals, e.g. LiMn2O4 or LiMn2OxFy
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
    • H01M4/52—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of nickel, cobalt or iron
    • H01M4/525—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of nickel, cobalt or iron of mixed oxides or hydroxides containing iron, cobalt or nickel for inserting or intercalating light metals, e.g. LiNiO2, LiCoO2 or LiCoOxFy
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to an electrolyte comprising a non-ionic surfactant and to a lithium ion battery using the same, and more particularly, to a non-aqueous electrolyte for a lithium ion battery comprising a fluorine-based non-ionic surfactant.
  • the lithium ion liquid secondary battery comprises an anode including carbonaceous material as an anode active material and a cathode including metal oxide of lithium cobalt oxide (LiCoO 2 ), etc., as a cathode active material, and is prepared by intercalating a porous polyolefin-based separator between the anode and the cathode, then by injecting a non-aqueous electrolyte having a lithium salt of lithium hexafluorophosphate (LiPF 6 ), etc.
  • LiPF 6 lithium hexafluorophosphate
  • the lithium ions of the cathode active material are released and then inserted into the carbon layer of the anode.
  • the opposite occurs with the lithium ions of a carbon layer of an anode being released and then inserted into the cathode active material.
  • the non-aqueous electrolyte plays a mediating role moving the lithium ions between the anode and the cathode.
  • the electrolyte should be stable within the scope of the operation voltage of the battery, and be able to transfer the ions sufficiently at a fast velocity.
  • U.S. Pat. Nos. 5,521,027 and 5,525,443 discloses an admixture electrolyte of a linear carbonate and cyclic carbonate.
  • the cyclic carbonate has a large polarity and thus is sufficiently capable of dissociating lithium, but has high viscosity.
  • linear carbonate with a low polarity and a low viscosity reduces the viscosity of the electrolyte comprising the cyclic carbonate.
  • the different linear carbonates include dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC), etc.
  • the different cyclic carbonates include ethylene carbonate (EC), propylene carbonate (PC), vinylene carbonate (VC), butylene carbonate (BC), etc.
  • the use of cyclic carbonates is necessary when it is desired to obtain a light capacity, good temperature properties, and a safe battery configuration, and particularly, when using electrolytes having a high viscosity such as EC, PC, etc.
  • the non-aqueous electrolyte decreases operational efficiency because it is slowly penetrated into the active material of electrodes, and thus the performance of the battery deteriorates by increasing an impedance thereof because a sufficient capacity of the battery cannot be utilized. Accordingly, in order to improve an interfacial property between the non-aqueous electrolyte and electrodes, Japanese Patent Publication Hei 8-306386 discloses a method of adding an anionic surfactant to an electrolyte and Japanese Patent Publication Hei 9-30651 discloses a method of adding an anionic surfactant directly to the electrode slurry. However, satisfactory results have not been obtained with these two methods.
  • the surfactant that is contained in an electrolyte should not affect the other properties of a battery, should be stable in the operation voltage range of a battery and increase an interfacial activity between electrodes and an electrolyte.
  • the present invention was made in consideration of the problems of the prior art, and it is an object of the present invention to provide an electrolyte additive comprising a fluorine-based non-ionic surfactant, which can improve impedance properties of a battery by improving an interfacial property between an electrolyte and electrodes, and which can be used in preparing a lithium ion secondary battery having a high capacity and high efficiency.
  • the fluorine-based non-ionic surfactant is represented by Formula 1 as follows: wherein, R is a hydrogen, an acetyl group, a methyl group or a benzoyl group; and m and n are integers from 2 to 20.
  • the surfactant can be used in the preparation of a lithium ion battery having high capacity and high efficiency.
  • the lithium ion battery comprises: an anode active material; a cathode active material; a porous separator; and an electrolyte.
  • the electrolyte comprises a lithium salt; an electrolyte compound; and the fluorine-based non-ionic surfactant represented by Formula 1 above.
  • FIG. 1 is a graph comparing impedance properties of lithium ion batteries prepared according to Examples 19-24 and of batteries prepared according to Comparative Example 2;
  • FIG. 2 is a graph comparing impedance properties of lithium ion batteries prepared according to Examples 25-30 and of batteries prepared according to Comparative Example 2;
  • FIG. 3 is a graph comparing impedance properties of lithium ion batteries prepared according to Examples 35-36 and of batteries prepared according to Comparative Example 2.
  • the present invention relates to an electrolyte comprising a fluorine-based non-ionic surfactant represented by Formula 1 below: wherein, R is a hydrogen, an acetyl group, a methyl group or a benzoyl group; and m and n are integers from 2 to 20.
  • the present invention provides a lithium ion secondary battery comprising an anode including graphitized carbon, a cathode including lithium-containing transition metal oxide, a porous separator and an electrolyte containing a fluorine-based non-ionic surfactant represented by Formula 1 above, in which the secondary battery has a large capacity and improved impedance properties.
  • EC which is a cyclic carbonate used for a battery employing a graphitized carbon anode
  • EC which is a cyclic carbonate used for a battery employing a graphitized carbon anode
  • it rapidly decreases low temperature properties of an electrolyte because it has a melting point that is higher than room temperature.
  • 2-ingredient electrolytes containing linear carbonates having a low melting point and a low viscosity have generally been used.
  • the present invention can decrease an impedance of the whole cell by adding a fluorine-based non-ionic surfactant represented by Formula 1 to an electrolyte such that the easy penetration of an electrolyte into electrodes occurs to decrease interfacial resistance.
  • the surfactant added should not affect the other properties of the battery and should be stable in the operation voltage range of the battery.
  • the surfactant, represented by Formula 1 used in the present invention is a high molecular compound substituted at each hydroxy group of its end group with acetyl, methyl or a benzoyl group by a common organic synthetic process in order to eliminate reactivity with an electrolyte.
  • the fluorine-based non-ionic surfactant represented by Formula 1 has a hydrophobic group using a fluorocarbon ring instead of a hydrocarbon ring, which is resistant to heat and chemicals since it has strong carbon-fluorine bonds, and particularly which does not affect the other properties of the battery since it remains stable during charging/discharging of a battery.
  • one end of the surfactant that is covered with fluorocarbon has a much higher interfacial tension at a surface of a solid electrode to improve the interfacial properties between a solid electrode and an organic solvent.
  • the present invention prepares a lithium ion secondary battery having a large capacity and improved impedance properties using an electrolyte comprising a fluorine-based non-ionic surfactant represented by Formula 1 above.
  • the lithium ion battery of the present invention comprises a graphitized carbon that can reversibly store and release lithium as an anode active material; lithium-containing transition metal oxides that can reversibly store and release lithium as a cathode active material; a porous separator; and a non-aqueous electrolyte comprising a lithium salt, an electrolyte compound and a fluorine-based non-ionic surfactant represented by Formula 1 above.
  • the graphitized carbon has preferably an interplanar spacing of d002 of 0.338 nanometers (nm) or less as measured by X-ray diffraction of carbonaceous material, and has a specific surface area of 10 squared meters per gram (m 2 /g) or less as measured by the Brunauer-Emmett-Teller (BET) method.
  • the lithium-containing transition metal oxide is preferably selected from the group consisting of LiCoO 2 , lithium nickelate (LiNiO 2 ), lithium manganese oxide (LiMn 2 O 4 ), and LiNi 1-x Co x O 2 (0 ⁇ 1).
  • the lithium salt is preferably at least one selected from the group consisting of lithium perchlorate (LiClO 4 ), lithium trifluoromethane sulfonate (LiCF 3 SO 3 ), LiPF 6 , lithium tetrafluoroborate (LiBF 4 ), lithium hexafluoroarsentate, (LiAsF 6 ), and lithium (bis) trifluoro methane sulfonimide (LiN(CF 3 SO 2 ) 2 ).
  • LiClO 4 lithium trifluoromethane sulfonate
  • LiPF 6 lithium tetrafluoroborate
  • LiAsF 6 lithium hexafluoroarsentate
  • LiN(CF 3 SO 2 ) 2 lithium (bis) trifluoro methane sulfonimide
  • the electrolyte compound is preferably selected from the group consisting of ethylene carbonate, propylene carbonate, butylene carbonate, vinylene carbonate, diethyl carbonate, dimethyl carbonate, ethyl methyl carbonate, gamma-butyrolactone, sulfolane, methyl acetate, and methyl propionate.
  • the contents of the fluorine-based non-ionic surfactant represented by Formula 1 is preferably 0.01 to 1weight percent (wt %) of the electrolyte.
  • the battery using the components as mentioned above uses, for example, an anode comprising carbon active material and a polyvinylidene difluoride binder, and a cathode comprising lithium transition metal oxide active material, conductive carbon and a polyvinylidene difluoride binder to realize a lithium ion battery.
  • the present invention prepares a lithium ion battery using a fluorine-based ethylene oxide surfactant represented by Formula 1 above, thereby enabling the sufficient penetration of an electrolyte into the active material of a battery to decrease the impedance in the battery. This increases the capacity of the active material and charge/discharge efficiency.
  • Dimethyl sulfate (0.35 mL) was added thereto at a rate of 3 drops per 5 minutes. The mixture was further stirred in a bath at 65° C. for 3 hours.
  • Dimethyl sulfate (0.21 mL) was added thereto at a rate of 3 drops per 5 minutes. The mixture was further stirred in a bath at 65° C. for 3 hours.
  • electrolytes of Examples 13 -18 were prepared by the same method as in Examples 7-12.
  • Example 1 Except for the injection of the electrolyte prepared in Comparative Example 1, a lithium ion battery was prepared by the same method as in Example 1. A charge/discharge test was performed by the same method as in Example 1, the results of which are presented in Table 1.
  • Example 19 142d-Ac 0.1 3.81 89.81
  • Example 20 144d-Ac 0.1 3.80 89.38
  • Example 21 142d-Me 0.1 3.82 88.25
  • Example 22 144d-Me 0.1 3.84 88.96
  • Example 23 142d-Bz 0.1 3.83 88.75
  • Example 24 144d-Bz 0.1 3.82 88.75
  • Example 25 142d-Ac 0.01 3.80 88.97
  • Example 26 144d-Ac 0.01 3.78 89.62
  • Example 27 142d-Me 0.01 3.89 89.14
  • Example 28 144d-Me 0.01 3.78 86.61
  • Example 29 142d-Bz 0.01 3.72 87.35
  • Example 30 144d-Bz 0.01 3.79 88.59
  • the batteries prepared in Examples 19-30 and Comparative Example 2 were charged to 4.2 V and discharged to 3.0 V. The process was repeated, and the batteries were then charged again to 4.2 V and an impedance of the batteries was measured.
  • the impedance was measured by scanning from 1 MHz to 1 mHz (millihertz) using a Potentiostat/Galvanostat, Model 273A from EG & G PRINCETON APPLIED RESEARCH Company and the SI 1260 Impedance/Gain-phase analyzer from Solatron Instruments Company. The results of the measurements are presented in FIGS. 1 and 2 .
  • Lithium ion batteries were prepared using the electrolytes of Examples 33 and 34, respectively, by the same method as in Example 19.
  • the lithium ion battery prepared according to the present invention uses an electrolyte comprising a fluorine-based non-ionic surfactant substituted with various functional groups at the end as represented by Formula 1 above, improves the interfacial property between an electrolyte and electrodes, improves the impedance properties, and exhibits a high capacity and excellent charge/discharge properties.

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US10/380,141 2001-05-09 2002-05-08 Electrolyte comprising non-ionic surfactant and lithium ion battery using the same Expired - Fee Related US6960410B2 (en)

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KR10-2001-0025312A KR100446659B1 (ko) 2001-05-09 2001-05-09 비이온성 계면활성제를 포함하는 전해액과 이를 이용하는리튬이온 전지
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US20060204856A1 (en) * 2005-02-18 2006-09-14 Ryu Young-Gyoon Organic electrolytic solution and lithium battery employing the same
US20070020529A1 (en) * 2005-07-20 2007-01-25 Ryu Young-Gyoon Organic electrolytic solution and lithium battery employing the same
US20090029800A1 (en) * 2007-07-25 2009-01-29 Jones David D Golf Clubs and Methods of Manufacture
DE102009058606A1 (de) 2009-12-17 2011-06-22 Li-Tec Battery GmbH, 01917 Lithium-Ionen-Batterie
US20110233459A1 (en) * 2010-03-25 2011-09-29 E. I. Du Pont De Nemours And Company Mixture of polyfluoroalkylsulfonamido alkyl amines
US20110232924A1 (en) * 2010-03-25 2011-09-29 E. I. Du Pont De Nemours And Company Surfactant composition from polyfluoroalkylsulfonamido alkyl amines
US20110237834A1 (en) * 2010-03-25 2011-09-29 E. I. Du Pont De Nemours And Company Polyfluoroalkylsulfonamido alkyl halide intermediate
US8258341B2 (en) 2009-07-10 2012-09-04 E.I. Du Pont De Nemours And Company Polyfluorosulfonamido amine and intermediate
US9178250B2 (en) 2010-08-20 2015-11-03 Leclanche' Sa Electrolyte for a battery
US20150370171A1 (en) * 2013-01-29 2015-12-24 3M Innovative Properties Company Surfactants and methods of making and using same
US10347934B2 (en) 2014-09-26 2019-07-09 Ut-Battelle, Llc Shear activated impact resistant electrolyte
US10347945B2 (en) 2017-12-08 2019-07-09 Ut-Battelle, Llc Stabilized shear thickening electrolyte
US10637100B2 (en) 2018-04-20 2020-04-28 Ut-Battelle, Llc Fabrication of films and coatings used to activate shear thickening, impact resistant electrolytes

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WO2018033200A1 (en) * 2016-08-16 2018-02-22 Toyota Motor Europe Fluorinated ionic liquids with high oxygen solubility for metal-air batteries
US11380879B2 (en) 2017-07-10 2022-07-05 Nanoscale Components, Inc. Method for forming an SEI layer on an anode
KR102271678B1 (ko) * 2017-08-11 2021-07-02 주식회사 엘지에너지솔루션 비수성 전해액 및 이를 포함하는 리튬 이차전지

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US20090029800A1 (en) * 2007-07-25 2009-01-29 Jones David D Golf Clubs and Methods of Manufacture
US8258341B2 (en) 2009-07-10 2012-09-04 E.I. Du Pont De Nemours And Company Polyfluorosulfonamido amine and intermediate
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US20110237834A1 (en) * 2010-03-25 2011-09-29 E. I. Du Pont De Nemours And Company Polyfluoroalkylsulfonamido alkyl halide intermediate
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CN1503995A (zh) 2004-06-09
KR20020085676A (ko) 2002-11-16
CN1227760C (zh) 2005-11-16
WO2002091497A3 (en) 2005-06-09
EP1559149B1 (en) 2012-05-23
JP2004525495A (ja) 2004-08-19
EP1559149A2 (en) 2005-08-03
US20030170547A1 (en) 2003-09-11

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